Hydrochloric Acid → 5-(p-Ethoxycarbonylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine hydrochloride

HRID 22540Notes

Reaction equation

HRID 22540 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]3[CH:18]=[N:19][CH:20]=[C:16]3[CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[ClH:21].[H][H]>C(O)C.[Pd]>[ClH:21].[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]2[N:17]3[CH:18]=[N:19][CH:20]=[C:16]3[CH2:15][CH2:14][CH2:13]2)=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13649431ethyl 4-(H-imidazo[1,5-a]pyridin-5-yl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 136882145-(p-Ethoxycarbonylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.0 g of 5-(p-ethoxycarbonylphenyl)imidazo[1,5-a]pyridine in 120 ml of anhydrous ethanol containing 30 ml of concentrated hydrochloric acid, is hydrogenated with 1.0 g of 10% palladium on charcoal at 40 psi hydrogen and 60° for 4 h. The catalyst is filtered and the solvent is evaporated to yield a solid which is recrystallized from isopropanol and ether to provide the title compound, m.p. 164°-166°.

Workup

  1. filtrationThe catalyst is filtered
  2. customthe solvent is evaporated
  3. customto yield a solid which
  4. customis recrystallized from isopropanol and ether

Sources & evidence

ORD record
ord-61c67037ac2f4757993d22683604daf3
Source dataset
uspto-grants-1995_06
Patent number
US05428160

Reaction notes

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